Location: Windermere
Do Not Show Listings
8236 PROCIDA ISLE LN, WINDERMERE, FL 34786
$1,190,00052 Days on yellowkey MLS ID: O6383546
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4176 Built: 2018Monthly Fee: $299 Tax: $12,887 (2025)Community: Windermere Isle Ph 2Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,887
Elementary School: Castleview Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: This house is the perfect blend of luxury, comfort and modern convenience. From the moment you arrive, you're welcomed by a charming brick paver front porch that leads into a light-filled foyer with a private office at the front of the home. Beautiful wood-look tile flooring flows seamlessly throughout the main level. The stunning gourmet kitchen features 42” cabinets, gas appliances, light granite countertops, subway tile backsplash, a unique coffee bar nook with extra storage, and a spacious walk-in pantry with upgraded shelving—perfect for organization and functionality. Downstairs also offers a private bedroom and full bath with an oversized walk-in shower, ideal for guests or multigenerational living. Upstairs, you’ll find a versatile lounge area and four additional spacious bedrooms. The luxurious primary suite boasts a spa-like shower, upgraded vanity with extra storage, and a large walk-in closet complete with custom shelving. The upstairs laundry room includes enhanced shelving for optimal organization. Step outside to your screened-in private lanai overlooking a sparkling saltwater pool with heater, surrounded by mature landscaping that creates your own backyard oasis. Additional premium upgrades include EV outlet and charger, upgraded garage flooring, and a saltwater pool system for easy maintenance. Located in a vibrant community offering social events, a community pool, and playground—and situated near top-rated schools—this home is just a short drive from Disney property, making it perfect as a primary residence or vacation retreat.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Babi Hennemann (407-633-0777)
5106 TILDENS GROVE BLVD, WINDERMERE, FL 34786
$1,700,0005 Days on yellowkey MLS ID: O6397273
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4572 Built: 2006Monthly Fee: $317 Tax: $12,584 (2025)Community: Tildens Grove Ph 02Spa: YesSingle Family
Taxes:$12,584
Elementary School: Windermere Elem
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: PARADISE…FOUND. Welcome to this incredible custom-built executive home in Windermere’s esteemed & highly desired Tildens Grove community which welcomes you with 24-hour guard gated security and beautiful quiet tree-lined streets. Get ready for LUXURY around every corner of this home spanning nearly 6,000 square feet of indoor & outdoor living space. Starting with one-of-a-kind curb appeal, this gorgeous home sits on a large lot measuring ½ acre with endless views of beautiful greenspace & water, mature trees & extensive landscaping…peace, privacy & serenity are all yours. Live the Florida lifestyle OUTDOORS in your fully screened resort style saltwater pool & spa with an oversized travertine lanai patio complete with summer kitchen…an incredible outdoor living space ideal for entertaining or enjoying in solitude. The fantastic & flexible floor plan begins with solid wood six lite double entry doors into a grand welcoming foyer which flows directly into the large living spaces. Extremely tall ceilings on both first & second floors with stunning coffered trim details in each room and TONS of gorgeous windows & natural light throughout. The incredible gourmet kitchen is the HEART of this home featuring a large center island, custom cabinetry, recently upgraded quartz countertops & backsplash, built-in appliances including wood-panel refrigerator, wine/beverage cooler, Fisher and Paykel double dishdrawers, walk-in pantry…for the professional chef or amateur, you couldn’t ask for more! Interior & Exterior Neutral Paint in 2022. Custom Closet Built-ins. Plantation Shutters Throughout. This functional floor plan features SIX (6) large bedrooms, FOUR (4) full bathrooms and ONE (1) half bath (four bedrooms & three full baths on first floor -- two bedrooms & one full bath PLUS huge bonus room with half bath & wet bar plumbing on second floor). Large laundry room with tons of built-in cabinets & storage spaces, desk area plus full-sized fridge/freezer. Oversized three car garage with built-in storage and large paver driveway for plenty of parking space. Whole House Aquasana Water Filtration System. Pet-Free Home. The PERFECT location -- you can be tucked AWAY FROM IT ALL, yet located just minutes from shopping, dining, golf and major highways and roadways for easy access to anywhere in Central Florida & beyond -- 18 miles to Downtown Orlando, 25 miles to Orlando International Airport (MCO), 9 miles to world-famous “Restaurant Row” and Arnold Palmer’s Bay Hill, 7 miles to Walt Disney World. In addition to the 24-hour guard gated security (one gate only for entry/exit), Tildens Grove offers a beautiful community park area with large playground, tennis & pickleball courts, basketball court & soccer field. A+ public schools plus options for Windermere Prep & Foundation Academy within minutes. This is THE ONE you have been waiting for…WELCOME HOME!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
715 MAGNOLIA ST, WINDERMERE, FL 34786
$1,250,0002 Days on yellowkey MLS ID: S5147648
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3390 Built: 1999 Tax: $5,631 (2024)Community: Windermere TownSpa: NoSingle Family
Taxes:$5,631
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: ADU A beautiful home located in the heart of downtown Windermere offering 4-bedrooms, 3-bathrooms, with a perfect blend of comfort and convenience. The house features hardwood floors throughout, and large sliders that open to a beautiful backyard. This is a great home for entertaining or relaxing. This property features a fully equipped ADU with one-bedroom, one-bathroom space, ideal for in-laws, guests, or use as a private office. Located minutes from boat ramps and local amenities. Please schedule your viewing today.
Listing is courtesy of: IRIS INTERNATIONAL (407-448-5085)
Listing Agent: Robert Trien (407-484-8474)
1703 ROBERTS LANDING RD, WINDERMERE, FL 34786
$1,520,000205 Days on yellowkey MLS ID: O6346120
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3288 Built: 1996 Tax: $17,269 (2024)Community: Roberts LandingSingle Family
Taxes:$17,269
Elementary School: Thornebrooke Elem
Remarks: This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent upgrades—including a new roof, new insulation, new tile floors, new kitchen cabinets and countertops, new stainless steel appliances, fresh interior and exterior paint, and updated lighting fixtures-add modern elegance throughout. The east-facing design bathes every room in golden sunsets, creating a warm and inviting atmosphere. Set on 1.4 acres with no mandatory HOA, the property boasts a huge driveway with space for RV or boat parking, along with a twin boat slip dock and covered boat house. Perfectly located near top-rated schools, shops, restaurants, attractions, and major roads, this home is ideal for those seeking the Floridian way of life—where swimming, fishing, jet skiing, and year-round relaxation are just steps from your back door.
Listing is courtesy of: INTERNATIONAL NETWORK REALTY (407-963-8539)
Listing Agent: Wui Keong Goh (407-963-8539)
4301 DOWN POINT LN, WINDERMERE, FL 34786
$2,950,0001 Day on yellowkey MLS ID: O6398366
Bed: 5 Bath: 4.0 Gar: 6 Liv Area Sq Ft: 7153 Built: 1983 Tax: $19,012 (2025)Community: Down Point SubSingle Family
Taxes:$19,012
Middle School: Chain of Lakes Middle
Remarks: Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Phil Mariani (407-257-3609)
6840 HELMSLEY CIR, WINDERMERE, FL 34786
$719,99966 Days on yellowkey MLS ID: S5142930
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2847 Built: 2009Monthly Fee: $129 Tax: $5,044 (2024)Community: Preston SquareSpa: NoSingle Family
Taxes:$5,044
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago — an exceptional offering in a premier Windermere community. Owner relocated .motivated seller. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.
Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)
Listing Agent: Eleanor Desimone (845-796-6951)
4309 SALTMARSH SPARROW DR, WINDERMERE, FL 34786
$825,00010 Days on yellowkey MLS ID: O6396295
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3697 Built: 2015Monthly Fee: $130 Tax: $8,724 (2025)Community: Stillwater Xings Prcl Sc-13 PhSpa: NoSingle Family
Taxes:$8,724
Remarks: Check out 4309 Saltmarsh Sparrow Dr, a residence featuring a partial flooring replacement that enhances its overall presentation. The kitchen is equipped with all stainless steel appliances and includes a functional island. The primary bedroom provides a walk in closet, while the primary bathroom contains double sinks and a separate tub and shower. An exterior covered patio extends to a fully fenced in backyard, creating defined outdoor space. This property includes updated finishes and functional living spaces. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
13304 BELLARIA CIR, WINDERMERE, FL 34786
$2,868,00014 Days on yellowkey MLS ID: O6391558
Bed: 6 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4920 Built: 2013Monthly Fee: $483 Tax: $30,699 (2025)Community: BellariaSpa: YesSingle Family
Taxes:$30,699
Remarks: Some residences are simply houses. Others are a statement. Welcome to Casa Pietra — an exceptional estate nestled within Bellaria, one of Windermere's most exclusive guard-gated communities, where only 64 homes share the privilege of calling this address home. Set on nearly ¾ of an acre with serene water views, this meticulously curated two-story residence offers just under 5,000 square feet of refined living space — 6 bedrooms + office, 6 full bathrooms, and a seamless open-concept floor plan designed for both grand entertaining and intimate everyday living. From the moment you arrive, the travertine-accented façade, symmetrical palm-lined circular driveway, and manicured grounds signal that this is no ordinary home. Step inside and the interiors reveal the same intentionality: soaring ceilings, wide-plank flooring, crown molding, a dramatic stone fireplace wall, custom built-in shelving, and floor-to-ceiling windows that flood every room with natural light — and frame the resort-style backyard like a living work of art. The gourmet kitchen is anchored by a generous island, custom cabinetry, Thermador stainless steel appliances, a butler's pantry, and an oversized walk-in pantry — a space where function and elegance coexist without compromise. The main-floor primary suite offers a private sanctuary with a spa-inspired bathroom designed for true restoration. Upstairs, a second primary suite with private balcony, morning kitchen, and dual custom walk-in closets provides a retreat within a retreat — along with three additional en-suite bedrooms and a loft lounge area. Outside, the resort-style pool and spa — recently resurfaced and elevated with fire bowls, deck tile, and a built-in summer kitchen — anchor a breathtaking backyard designed for the Florida lifestyle at its finest. An aerial view reveals the true scale of the grounds: a dramatic allée of mature palms flanking the pool terrace, generous green space, and total privacy secured by lush hedgerows on all sides. Additional highlights include a 3-car garage, home automation system, gas fireplace, full security system with cameras, wine refrigerator, and landscape lighting — all thoughtfully updated and impeccably maintained. Zoned for top-rated Orange County schools, minutes from Winter Garden Village, upscale dining, and with easy access to major roadways — Casa Pietra is a rare convergence of location, lifestyle, and lasting value. Elegance is not decoration. It is a way of being.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Caroline De Castro Marcellini (561-319-9009)
14383 CREST PALM AVE, WINDERMERE, FL 34786
$1,166,99079 Days on yellowkey MLS ID: G5107222
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3550 Built: 2026Monthly Fee: $245 Tax: $2,489 (2025)Community: Palms At WindermereSingle Family
Taxes:$2,489
Elementary School: Bay Lake Elementary
Remarks: One or more photo(s) has been virtually staged. ELLINGTON II - Our beautiful, huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42" cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. Triple sliding glass doors and an extended covered lanai. 4 Bedrooms upstairs with 2 full baths and loft, overlooking wooded area.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
14354 CREST PALM AVE, WINDERMERE, FL 34786
$1,119,99097 Days on yellowkey MLS ID: G5106241
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3542 Built: 2025Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Remarks: One or more photo(s) has been virtually staged. *Images shown are for illustrative purposes only* TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. 9' hidden sliding glass doors and a covered lanai. Downstairs flex room works well as an office or study with 2 additional bedrooms and a laundry room. Common areas upstairs include a spacious bonus room and a 6th bedroom with full bath
8724 PEACHTREE PARK CT, WINDERMERE, FL 34786
$850,000192 Days on yellowkey MLS ID: S5135795
REDUCED by $49,000 (5.5%) on 04/07/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3315 Built: 2015Monthly Fee: $216 Tax: $9,856 (2024)Community: Peachtree ParkSingle Family
Taxes:$9,856
Remarks: Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a boutique enclave of just 28 homes located directly across the street from Walt Disney World. This rare community blends exclusivity, charm, and convenience, offering the perfect setting for both everyday comfort and unforgettable moments. Crafted by Ashton Woods, this Bimini model radiates elegance and functionality at every turn. Step inside to discover wood floors throughout the first level, a private office with French doors, and a formal dining room enhanced with a butler’s pantry and wine cooler. Ideal for entertaining. The gourmet kitchen is the heart of the home, featuring quartz countertops, custom window seating in the breakfast nook, and premium appliances. Upstairs, the primary suite is a true retreat with French doors, a long shower, and a custom walk-in closet. Additional bedrooms include a second suite and a Jack-and-Jill layout, providing flexibility for family or guests. Outdoor living is exceptional, with over 1,000 sq. ft. of decking—including 600 sq. ft. under screen enclosure—overlooking a serene pond and untouched forest, perfect for morning sunrises or evening gatherings. Schedule your private showing today and experience firsthand why Peachtree Park is unlike anywhere else.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Marcelo Machado (321-939-3748)
13124 FILLY CT, WINDERMERE, FL 34786
$1,575,000353 Days on yellowkey MLS ID: O6303140
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3300 Built: 1989Monthly Fee: $46 Tax: $15,459 (2024)Community: FarmsSpa: NoSingle Family
Taxes:$15,459
Remarks: Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As you step up to the front entrance, you are greeted by beautiful water fountain. Once inside your living room with a wood burning fireplace welcomes you to your living room on the right. Continuing your way into the house, your inviting family room awaits with an eat in kitchen island completing the scene. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances and plentiful cabinetry. Retreat to the oversized owner’s suite with double walk-in closets, a luxurious master bathroom and a private sitting area overlooking the pool area. Enjoy an enclosed pool area and expansive backyard. There is also a second master suite with private bathroom and walk-in closet. At the opposite end of the family room there is a hallway leading to another full bathroom and three additional bedrooms. Located just minutes from championship golf courses, downtown Windermere, Winter Garden Village, and top-rated schools, this home offers the perfect blend of tranquility and convenience. Don’t wait, schedule your showing today!
Listing is courtesy of: HOME N OFFICES INTERNATIONAL (407-864-4590)
Listing Agent: Marcelo Brandao (407-864-4590)
14347 CREST PALM AVE, WINDERMERE, FL 34786
$1,108,990390 Days on yellowkey MLS ID: G5094526
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 2025Monthly Fee: $275 Tax: $1,309 (2023)Community: Palms At WindermereSingle Family
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Under Construction. Step into refined living with this exceptional 4-bedroom, 4-bath residence spanning 3,123 square feet of impeccably designed space. Showcasing a sophisticated open-concept layout, this home offers the perfect balance of elegance and functionality. The main level impresses with soaring 10-foot ceilings and seamless laminate flooring, creating a bright, expansive ambiance. The gourmet kitchen is a true showpiece, featuring striking quartz countertops, an oversized island, and abundant custom cabinetry—ideal for both intimate gatherings and grand entertaining. Upstairs, a spacious bonus room with a full bath provides a private and versatile retreat, perfect for a media lounge, guest suite, or executive home office. Indulge in the beautifully designed primary bath, showcasing a spa-inspired walk-in shower with an oversized rain shower and a sophisticated dual vanity—creating the perfect blend of comfort and elegance. An oversized garage adds convenience and ample storage, completing this thoughtfully designed home that exudes modern luxury at every turn.
3328 WAX BERRY CT, WINDERMERE, FL 34786
$925,000167 Days on yellowkey MLS ID: O6355868
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2636 Built: 1984Monthly Fee: $21 Tax: $10,867 (2024)Community: Lake Butler EstatesSingle Family
Taxes:$10,867
Remarks: One or more photo(s) has been virtually staged. Located in Lake Butler Estates, one of Windermere’s most private established communities, this 4-bedroom, 4-bath single-family pool home sits on a 1-acre cul-de-sac lot surrounded by mature oak trees and lush landscaping, with only 11 neighboring homes and access to the Butler Chain of Lakes through the community’s private boat ramp. Built in 1959 and renovated in 2022, this single-story residence offers an open split floor plan, combining luxury finishes with functional everyday living. Interior features include marble flooring throughout the main living areas and engineered hardwood flooring in all bedrooms, high ceilings, crown molding, recessed LED lighting. The living room features a textured accent wall, skylights, and a wood-burning stone fireplace with gas connection that anchors the main living space. The kitchen was redesigned with sealed butcher block counters, stainless steel Samsung appliances, pantry storage, breakfast bar seating, reverse osmosis water treatment system, Samsung dishwasher, Samsung smart oven, pot filler, and a Fotile range hood with self-adjusting capture shield, with both kitchen water and irrigation supplied by well water. A dry bar adds additional entertaining appeal in the living room, while remote-controlled ceiling fans and lights are installed in every bedroom, with new chandeliers in the living and dining rooms. The spacious primary suite includes custom walk-in closet storage with overhead recessed lighting, sliding glass shower enclosure, Kohler rainfall shower, three-head body sprayers with jets, pebble flooring, marble backsplash, dual vanities, soft-close cabinetry, and bidet hookup. The shared bath offers dual sinks, LED anti-fog mirror, pool access, marble finishes, accent wall tile, pebble flooring, and dual shower heads. A newly added full guest bath includes Swiss Madison pedestal sink, Hansgrohe faucet, medicine cabinet, marble finishes, pebble flooring, and Kohler dual shower sprayers, while the en-suite bath in the first bedroom features sliding glass shower doors, marble backsplash, skylight, LED anti-fog mirror, and soft-close cabinetry. Smart-home and energy efficient features include Ecobee smart thermostat, myQ garage opener, smart front door lock, remote-controlled lighting systems and upgraded electrical outlets throughout. Exterior highlights include a screen-enclosed in-ground pool, covered lanai, outdoor workshop, circular driveway, side-entry two-car garage, extended parking pad, and additional rear concrete parking for RV or boat storage. The backyard offers expansion flexibility, allowing room for privacy fencing, a future mother-in-law suite, or an addition. The annual HOA is only $253 and includes access to the adjacent Windermere Recreation Center, offering 3 lighted tennis courts, fenced playground, pet parks, lakefront boardwalk, kayak launch, sand volleyball court, grills, picninc tables and large entertaining pavilion. Zoned for A-rated Windermere schools. Location second to none as this home is within 10 minutes of downtown Windermere where you can enjoy the weekly Farmers Market. Easy access to Interstate 4, Florida Turnpike, local hospitals, and within 30 minutes of Orlando International Airport, Disney World, and Universal Studios. This move-in-ready Windermere property delivers privacy, acreage, and premier community access in one of Central Florida’s most desirable residential corridors. Schedule your showing today!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Ferris Kassar (407-284-8384)
8337 VIVARO ISLE WAY, WINDERMERE, FL 34786
$800,000201 Days on yellowkey MLS ID: O6332989
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3294 Built: 2018Monthly Fee: $268 Tax: $6,438 (2024)Community: Windermere IsleSpa: NoSingle Family
Taxes:$6,438
Remarks: Discover your dream home in the highly sought Windermere Isle community, just minutes from the world-renowned Disney attractions. This stunning residence offers an unparalleled blend of comfort, convenience, and elegance, making it an ideal choice for families and those who love to entertain. Boasting five spacious bedrooms and four well-appointed bathrooms, this home provides ample space for family and guests. The thoughtful floor plan includes a first-floor bedroom and full bath, perfect for visitors seeking privacy. The oversized owner's suite offers a private retreat, while the loft area adds versatility to the living space. One of the home's standout features is its exceptional storage capacity, a rare find in Florida. The freshly painted exterior and meticulously maintained interior create a like-new ambiance, with elegant touches such as a separate dining room with a coffered ceiling, perfect for formal gatherings or as a flexible office space. The serene setting of this property is truly captivating, with a tranquil pond view that enhances the sense of retreat and relaxation. The extended lanai and expansive backyard provide the perfect backdrop for outdoor activities, entertaining, or simply unwinding in the Florida sunshine. The open floor plan seamlessly connects the gourmet kitchen, breakfast nook, and family room, offering a harmonious space for daily living and hosting guests. Windermere Isle offers a host of community amenities, including a neighborhood pool with cabana, playground, and walking paths. The HOA ensures easy living by providing lawn maintenance, internet, and cable services. Located near top-rated public and private schools, SR 429, and the vibrant dining and shopping options of Horizon West, this home offers the perfect balance of a peaceful neighborhood setting with the convenience of nearby urban amenities. This property is a rare gem in today's market, combining a desirable location, generous living space, and a picturesque setting. Don't miss your chance to call this exceptional residence your new home. Contact me today to schedule a private viewing before it's gone!
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Laurel Kellett (407-758-1136)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00044 Days on yellowkey MLS ID: S5144606
REDUCED by $10,000 (0.7%) on 04/12/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $8,883 (2024)Community: Windsor HillSingle Family
Taxes:$8,883
Remarks: Situated on a premier half-acre lot in highly desirable area of Windermere, this fully renovated 4-bedroom, 4-bath home offers a hard to find 'like-new' living experience. Every detail has been thoughtfully updated, featuring a chef’s kitchen with brand-new Thermador appliances, custom cabinetry, luxury vinyl plank flooring, and designer lighting throughout. The versatile floor plan includes an oversized upstairs bonus room, perfect for a media retreat or home office. Modern systems provide complete peace of mind, including a 2021 roof, dual high-efficiency A/C units, new water heater, and new sliding doors opening to the expansive backyard. An epoxy-finished garage adds style and convenience. Just minutes from the Butler Chain of Lakes, top-rated schools, and world-class golf, this move-in-ready home blends refined design with modern comfort.
Listing Agent: Jessica Oliveira (407-925-9768)
13525 GORGONA ISLE DR, WINDERMERE, FL 34786
$1,120,00056 Days on yellowkey MLS ID: O6377789
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4625 Built: 2018Monthly Fee: $268 Tax: $9,351 (2025)Community: Windermere IsleSpa: NoSingle Family
Taxes:$9,351
Remarks: One or more photo(s) has been virtually staged. Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless entertaining. A dramatic two-story foyer creates a striking first impression, highlighted by a custom hardwood staircase with decorative iron balusters. Architectural details continue throughout with 9.5-foot ceilings, 8-foot doors, coffered ceilings, porcelain tile on the main level, and hardwood flooring upstairs. Custom Disney-inspired stained-glass window inserts throughout the home offer a subtle and charming nod to the nearby magic. The expansive open-concept living area is anchored by a chef-level gourmet kitchen featuring a natural gas cooktop, dual convection ovens, quartz countertops and backsplash, oversized island, 42-inch cabinetry, café dining area, and walk-in butler’s pantry—perfect for entertaining and daily convenience alike. The main-level primary suite serves as a tranquil retreat with a spa-style bathroom, soaking tub, glass-enclosed walk-in shower, and generous custom closet. Upstairs, five additional bedrooms include a private guest suite and well-designed shared layouts, along with a spacious upper-level great room and reading nook ideal for a media room, game space, or lounge. Significant upgrades include a 27kW commercial-grade whole-house generator, tankless water heater, gas dryer, advanced humidification and UV air filtration, and a garage with custom cabinetry, overhead storage, and durable polyaspartic flooring. Energy-efficient systems and abundant natural light enhance comfort throughout. The lot to the right of the home is Protected Green Space in perpetuity and cannot be developed so you will always have that space. Seller is providing a credit towards a 2-1 RATE BUY DOWN with full price offer. Inquire for more details.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Roo Klaers (407-493-5615)
6133 S HAMPSHIRE CT, WINDERMERE, FL 34786
$3,150,0004 Days on yellowkey MLS ID: O6397043
0 Days Off yellowkey (back on 4/11/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6335 Built: 2000Monthly Fee: $298 Tax: $35,657 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$35,657
Remarks: Under contract-accepting backup offers. Sophisticated Elegance best describes this stunning remodeled 5 Bedroom/5FULL Bath/2 Half bath Golf Course Estate Home in Keene’s Pointe. Upon entering this residence built by master custom builder J. Richard Watson, you will discover the seamless beauty of the 48 x 24 tiles that grace the entire main floor and set the tone for this gorgeous interior space filled with abundant natural light. Your eyes are drawn to the impressive living and dining rooms that meld together in this open concept while already eyeing the dramatic Family Room view through a graceful arched cast stone passage into the “heart of the home”. The remodeled kitchen and family room display an elevated level of design rarely seen today, equipped with new cabinetry and accent lighting accentuating the Cambrian custom countertops and back splash areas and new appliances by Wolf, Sub-Zero and Cove. The adjacent Family Room has a clever hospitality bar hidden behind tall double doors so discreet and refined that you are delightfully surprised when you open them to see the mirrored walls and lighted cabinets storing sparkling glasses and a wine refrigerator! Attractive fireplace framed out in a custom Cambria surround is flanked by matching accent walls to feature your most cherished collectibles. From the foyer to the kitchen, you note several coordinated glass and gold chandeliers that highlight the ivory walls, fresh interior paint and new can lighting and ceiling fans throughout. You will also find a large study, the primary retreat and a guest-ensuite bedroom on the main floor. Just off the kitchen, a lovely staircase beckons you up to a mid-level reimagined home theatre with the latest in sight, sound and special effects. New plush red leather recliners are enhanced with vibrations that mimic the main event on the screen to make you feel like you are in it – not just watching! Other rewards include the private half bath, beverage bar, professional popcorn machine and extra seating to enjoy the ambiance without leaving the room! Continuing up the staircase you will discover the second floor featuring 3 bedrooms, 2 Full Baths: (1 ensuite and 2 bedrooms sharing an oversized bathroom with dual vanities, and soaring ceiling with skylight!) Both the enormous bonus room and the ensuite bedroom open to a screened balcony overlooking the pool, golf course and the nature preserve in the distance. Second floor is all engineered hardwood throughout and all bathrooms are renovated. The spacious outdoor screened living area is impressive as well, with a large pool with pebble tec finish tucked within so easy to maintain its pristine sparkle keeping nearby oak tree leaves out of bounds! Enjoy the built-in fire pit and conversation area, along with a separate wet bar under the covered lanai. There is an additional summer kitchen featuring a natural gas grill and built in “Green Egg” allowing you to manage most any cookout gathering! Finally, light up any event you host any day of the year with the custom Massey Outdoor Landscape Lighting color carousel that allows you to choose your color for any seasonal holiday simply by pressing your app! So, sit back and enjoy the view of the wide eighth fairway of the renown Jack Nicklaus Signature Golf Course in Keene’s Pointe. Come live the lifestyle for which Keene’s Pointe is famous and add just an extra splash of refined elegance to the mix!
Listing is courtesy of: KEENE'S POINTE REALTY (407-876-8879)
Listing Agent: Angela Durruthy (407-496-5811)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$3,500,00076 Days on yellowkey MLS ID: O6377244
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Monthly Fee: $103 Tax: $28,092 (2025)Community: LakesSpa: YesSingle Family
Taxes:$28,092
Remarks: Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
13734 LAKE CAWOOD DR, WINDERMERE, FL 34786
$1,390,00068 Days on yellowkey MLS ID: G5107723
2 Days Off yellowkey (back on 4/11/2026)
REDUCED by $110,000 (7.3%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4437 Built: 2006Monthly Fee: $172 Tax: $11,421 (2024)Community: Lake Cawood EstatesSingle Family
Taxes:$11,421
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. NEW PRICE - SELLER MOTIVATED! Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a three-car garage and exceptional privacy. A long driveway and inviting covered front porch create a warm welcome, while soaring ceilings and tranquil pool views greet you the moment you step inside. The open floor plan is ideal for entertaining and everyday living, featuring a grand living room with gas fireplace, formal dining room with wet bar, expansive family room, and a versatile game or bonus room perfect for a media space, home office, or guest retreat. The gourmet kitchen opens seamlessly to the breakfast nook and family room and is beautifully appointed with granite countertops, stainless steel appliances, built-in double ovens, and a large center island. The luxurious primary suite offers tray ceilings, a private fireplace, sitting area, and abundant natural light, along with a spa-inspired ensuite featuring dual vanities, a jacuzzi tub and two spacious walk-in closets. Three additional bedrooms are generously sized with large closets and a convenient cabana bath provides direct access to the outdoor living area. Step outside to your private resort-style retreat featuring a screened heated pool and spa, expansive paver patio, and a fully equipped summer kitchen designed for year-round Florida living and entertaining. Large sliding doors provide seamless indoor-outdoor flow, enhancing the home’s open and airy feel. Built in 2004 and extensively upgraded for modern comfort and peace of mind, this move-in-ready home features a brand-new roof (2024), new A/C system (2024), new well system (2025), new water filtration system, new saltwater pool system (2025), fresh interior paint (2025), updated lighting and fans (2024), and new kitchen and laundry appliances including a GE Café refrigerator and dishwasher and Samsung washer and dryer. The property operates on well and septic, providing efficiency and long-term value. Ideally located near top-rated dining, shopping, and everyday conveniences, this exceptional home is approximately 15 minutes from Walt Disney World and less than 30 minutes from Orlando International Airport. This rare opportunity combines luxury, space, and major system upgrades in one of Central Florida’s most desirable communities. Schedule your private showing today and experience the lifestyle you’ve been dreaming of.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Angela Schifano (407-953-7476)
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